Pokemon Matchmaker
by Golfer2012
Summary: After Ash returning to Pallet Town. Max, Dawn, Jessie and James planning to make a matchmaker for putting Ash and May together. This also include some Pokemon love. Will this going to be failed or success ? Main shipping are Advanceshipping and IceSparkshipping. Other shipping will be suggest.
1. Chapter 1

**Note: For this story, Jessie and James never join Team Rocket. Everything will be same for anime.**

**I don't own Pokémon (I wish). All characters, plot, anime etc are belongs to Game Freak.**

**Ash: 16, Misty and Iris: 17, Brock and Cilan: 18, Jessie and James: 20, May: 15, Dawn:14, Max: 13**

* * *

"Pikachu, finish it up with your Electro Ball!" shouted Ash. He had finally advanced to the finals in the Unova League. Their attack had shocked their opponent's Carracosta, which had given them their victory.

"Carracosta is unable to battle, that means the victors go to Ash Ketchum from Pallet Town, winner of the Unova League!"

"Yeah Pikachu! We did it!"

Pikachu ran towards Ash, giving him a hug for their victory. Iris and Cilan then came over to congratulate him of his win of the league.

After award ceremony:

Ash and his friends decided to rest at the Pokémon center.

"So Ash, what are you going to do after the winning the league?" Iris then asked while petting her Axew.

If you asked where Cilan was, he was making a phone call to his brothers.

"Well, I have to go back to Pallet Town to see my mom and friends, along with all of my Pokémon." explained Ash.

"How many Pokémon you have?"

"Let see, there was ten with me, three for training, three for release, twenty-two Pokémon that are with Professor Oak…so, I think I caught thirty-eight."

Both eyes widened of how many Ash caught already. Cilan walked in and barely heard everything that he said. "Wow, I am very impressed to know you caught that many Pokémon in many different regions." a surprised Cilan interjected.

"I also have traveled with my friends in every region. Heres all the photos with my friends!" said Ash. Each photo showed Misty, Brock from Kanto, Brock,May and Max from Hoenn, Brock, Dawn from Sinnoh, finally Jessie and James…for some reason.

Iris, Cilan, and Axew were amazed at the amount of Ash's friends and said that they would like to meet them.

"That great, but I guess there were no more going on the journey." a saddened Iris realized.

"Hey, I have idea, maybe you guys can come back with me to Pallet Town!"

"That's good idea. That only reason why I called my brothers was about going to Kanto."

"Axew axe!(Then we are all going to Kanto in Pallet Town!)" cried the Axew in its native tongue.

"Pika pika, Pikachu!(You will have a blast to meet all the Pokémon and great place to visit)".

"Then tomorrow, we are leaving to Kanto in Pallet Town!"

Everybody agreed, and with that regard, everyone had retired to their rooms…Expect Axew, who was confused to why Ash's face turned light red for mentioning May. He decided just wait for tomorrow to ask Pikachu.

* * *

**Wow another short chapter. Next chapter will be longer. I start to get use of different format. Only main shipping in this story are Advanceshipping and Rocketshipping. Also it will include some PxP. Jessie, James, Max, and Dawn planning to get Ash and may together, same for other Pokémon.**

**I really want to know which shipping you want to include for Brock, Misty, Dawn, Iris, Cilan, Max, Tracey, Gary, Drew, Harley, Paul, Zoey, Kenny, Barry, Conway, Trip, Stephan, Bianca, Georgia, Burgundy, or no one above. Next chapter, I will post a next chapter for picking which shipping wanted to include. For example: picking Shootdownshipping or Againstshipping.**

**It don't have to include on the list. It could pick like Brock x Holly. If you want me to add any character that are not on list, please tell me.**

**I not doing a Pokeshipping, Contestshipping, and Ikarishipping. Same for OCs, Yaoi and Yuri.**

**Ash will explains about Jessie and James in next chapter. Everything would be same in anime expect for not appearing in Unova.**

**Please Reviews and The Battle of Regions will be on hiatus until I'm getting 15 reviews.**

**Edit: Happy Advanceshipping Day. I didn't know it was on Nov 21. Sorry.**

**Edit: Refixing some the grammers and the beta reader helping me for this.**


	2. Chapter 2

**I never own any characters, plot, Pokémon, it belongs to Game Freak, Pokémon Company, Nintendo.**

* * *

_May's Dream_

_It was a quiet night in the Pallet Town for Ash and May. Outside of Oak's Lab, they watched the stars with their Pikachu and Glaceon peacefully sleeping beside their owner. They decided to spend some time with each other before leaving for different regions._

_"Um Ash, there is something I want to say." with that statement, it made a blushing May. "Go ahead, I'm listening." replied Ash. May looked into Ash's eyes and knew what he was going to say._

_"Ash, I wish I never had gone to Johto, because I miss you so much. I had been having feelings for you for long time. I love you Ash." _

_"I love you to May, I never stopped thinking about you while we were separated."_

_Both trainers looked in eachother's eyes, leaning closer to kiss. May's heart began racing as she closed her eyes and began to kiss. When both began to kiss, Ash instead licked her face. May opened one of her eyes with confusion._

_"Ash, why did you lick my face?"_

_"Nya."_

May then shot up, only realizing it was her Skitty meowing on her bed.

"Skitty, why you wake me up of having a wonderful dream?" sighed a now depressed May. She looked outside, and realized it morning.

"Nya Nyan Nyah! (It's time for breakfast May!)" purred the cheerful Skitty. Her Pokémon then left the room and waiting for her to arrive downstairs. She got out of the bed and got dressed.

It has been two months since May won the Johto Grand Festal. She had lost to Drew in Sinnoh. With that loss in mind, she planned on staying home for some training with her Pokémon. Her Brother got home from the journey and lost, placing in top 8 in the Hoenn League.

"Too bad my dream isn't real."

* * *

Back in Unova:

Ash, Iris, and Cilan just woke up in the early morning, ready and packed to leave the Pokémon center.

"Well Ash, it great to see you again. Congratulations on winning the Unova League!" an excited Juniper cheered.

"Thanks Professor!"

He then unhooked the Pokeballs from his belt, releasing the contents, while four others then came from a side door.

His Pokémon were the Normal Flying Type Unfezant, the Water Type Oshawott, the Fire Fighting Type Pignite, the Grass type Snivy, the Fighting Dark type Scraggy, the Bug Grass Type Leavanny, the Water Ground Type Palpitoad, the Rock Type Boldore, and the Dark Ground type, Krookodile.

They all smiled and happy to see their owner won the league. The four who didn't do the last battle still congratulated him with hugs.

"Hey guys, thank you so much. How about I take all of you to my place in Pallet Town?"

All of his Pokémon cheered, before He returned all of his Pokémon back to their Poke Balls and ready to go abroad.

* * *

Meanwhile, in Hoenn:

May, Max, and her parents just finished eating their breakfest. Norman and Caroline were washing the dishes, while May and Max fed the Pokémon outside.

Blazkien was working on his new move, Blast Burn with Wartortle and Glaceon watching to make sure nothing caught on fire. Beautifly and Skitty were playing each other. Venusaur and Munchlax were practicing their contest moves.

"Wartortle, war?(Are you going to tell Pikachu about your feelings?)" questioned the turtle Pokemon.

Glaceon blushed for the idea of having feelings toward Pikachu. Before she could reply, May and Max were her saving grace with their food.

"Guys! Breakfast is ready!" yelled May while she held the bowl with their food. All of her Pokémon stopped what they were doing before going to get something to eat. Max was keeping an eye on Munchlax, making sure he didn't eat everybody else's food.

"After they finish eating, we are all going to Pallet Town to celebrate his Unova League win."

She did notice her Glaceon a bit red in the face at the mention of Pallet Town.

"It's very hard to keeping secrets. I haven't told Ash about my feelings." mumbled a quiet May.

* * *

Ash and friends had already arrived at Ash's home, where he was showing the various picture frames that were on his wall.

"So, how about you talk about your friends?" asked Cilan while holding some of the pictures.

"Yeah! Tell us about your journey!" an excited Iris yelled. Ash smiled and reminisce.

"Misty was the Cerlean Gym Leader. She left the gym for becoming the world's greatest Water Pokémon Trainer. She had three sisters and hated bug types. I met her when I was just borrowing her bike to get away from flock of Spearows. We've been traveling to Kanto, The Orange Islands and Johto with her. She left after that journey in Johto because she had to go to gym while her sisters on vacation."

He then took a deep breath before continuing.

"Brock was my best friend since we travelled to all the different regions, expect for the Orange Islands. He was the former Pewter City Gym Leader. Brock always wanted to become a Pokémon Breeder. He was also a great cook and was great at taking care of his Pokémon. Brock would always fall in love with every girl he saw, especially Nurse Joy and Officer Jenny, but Misty, Max, and even his Croagunk dragged him is now trying to become a Pokémon doctor."

"Tracey was a Pokémon Watcher. He joined us during the Orange Islands. He was the main idol of Professor Oak. He liked to sketch about every Pokémon he saw. He knows a lot about that island. When I got my Lapras, we began traveling through the ocean. After our journey ended in the Orange Islands, Tracey decided to become Professor Oak's assistant."

"May was the best Pokémon Coordinator I've ever seen. She loves doing contests with her Pokémon. She used to dislike Pokémon, but I showed her compassion towards them. She was in the Top 8 in Hoenn's Grand Festival. Then we decided to travel the Kanto Region again so she can compete in the contests, while I complete the Battle Frontier. She was always nice, cute, and charming. Her brother Max, wasn't a Pokémon Trainer, but he knows everything about Pokémon types, battles, and skills. Sometimes he kind of goes overboard with the experiences."

"Lastly, Jessie and James. But this was different. They were former Team Rocket members. They decided to quit while under training. I met them while I was hurrying to Professor Oak's Lab to get my starter, then we met again to save us from Butch and Cassidy. They all decided to join us traveling to all the different regions. Sometimes they are with us most of the time. James always collects bottle caps and loves his Pokémon. Jessie entering contests in Hoenn, Kanto and Sinnoh. They decided to go to Johto complete in contest after traveling in Sinnoh."

After Ash was done talking about his friends (expect Dawn, because Iris and Cilan already met Dawn in Undella Town), Iris and Cilan were very surprised how many people Ash had met in those different regions. Axew saw Ash turn red when he was talking about May.

"Axew axe ax?(Hey Pikachu, why your trainer are blushing about May?" questioned the dragon type.

"Pika pi, Pikachu…(Well Ash does have a crush, but...)"

"Axe Axew?(Do you have a crush also?)"

Pikachu then blushed from thinking about Glaceon. He helped Glaceon a lot during their contest days.

"Pika chu chu?(Um, hey are those Wingull flying next to us?) said Pikachu.

"Axew?! Axew ax! (Really?! let me see!"

They looked out the window and saw those Wingulls flying next to the plane.

Ash looked over and saw Pikachu turning red as his cheeks, before sighing.

"It's very hard to keep a secret from everyone."

* * *

**Wow this was very long chapter and I think I like this one. I guess I didn't explain enoug for last chapter and hopeful this explain better. The main shipping will be include Advanceshipping, Rocketshipping. Here the polls.**

**For Misty: Gymshipping (Brock x Misty), Orangeshipping (Tracey x Misty), or SeaMonkeyshipping (Cilan x Misty)**

**For Dawn: Twinleafshipping (Barry x Dawn), Penguinshipping (Dawn x Kenney), Cavaliershipping (Gary x Dawn) or ShowOffshipping (Max x Dawn)**

**For Iris: Wishfulshipping (Iris x Cilan), Medicineshipping (Brock x Iris), **

**For Zoey: ShootDownshipping (Kenny x Zoey), Againstshipping (Paul x Zoey) or Emulateshipping (Barry x Zoey)**

**For Georgia: ****Hairflip**shipping (Drew x Georgia) or **OverArrogant**shipping (Paul x Georgia)

**For Burgundy: Burgundy x Paul, Burgundy x Drew or Burgundy x Trip**

**For Ursula: Mockshipping (Paul x Ursula), Egocentricshipping (Harley x Ursula) or Conway x Ursula**

**For Solidad: Defeatedshipping/Gossipshipping (Drew x Solidad) or KantoContestshipping (Harley x Solidad)**

**For Bianca: Spokeshipping (Stephan x Bianca), Hypershipping (Barry x Bianca) or Serviceshipping (Cilan x Bianca)**

**Should I include Handymanshipping (Tracey x Daisy) and Ritchie x Casey ?**

**That it. I just need some shipping suggestions. If something you want to add please PM or review Thank you for reading this and please ****review.**

**Edited: I add Iris to the list and names of the shipping and new shippings**


	3. Chapter 3

**I never own any Pokémon characters. It belongs to Game Freak.**

**This chapter will explain how Jessie and James become friends with Ash and quit Team Rocket early.**

It been two months since Jessie and James stopped traveling with Ash and went to compete in Johto's contests. Jessie was placed in the top 8 for grand festival. Jessie decided to go back to the Kanto and won the ribbon cup all thanks to her Pokémon Seviper, Dustox, Yanmega, and Jame's Carnivine. While traveling in different regions, they all reunited with their old Pokémon like Weezing, Arbok, Dustox, and Chimecho while they both caught Woobat and Yamask on way home from Kanto Grand Festival. James on the other hand decided to become a Pokémon Breeder since his friend Brock showed him a lot of different things with Pokémon.

'You know it's been four months since we travelled with Ash and his friends." said James while giving a bit of food to his Pokémon.

"Yeah, I'm sure Ash is still busy in Unova of collecting those badges." Meowth replied while playing with his yarn ball. Jessie did notice what they talking about. She smiled those days travelling with Ash and replied, "I'm sure he will do well in Unova. It reminds me of those good memories when we just met Ash and his friends."

_Flashback_

_This take during the episode called "Training Daze", when James got injured. Spoilers: If you don't know this or heard of it, I recommend seeing this episode before reading this._

_Jessie decide to go out for a walk in the forest when she lost her partner, which was 11 times. Meowth still followed Jessie to see is he could help her out of the sadness and pain._

_"So Jessie, what are we suppose to do now?" asked a worried Meowth._

_With her mind being blank and really not knowing what to do anymore, (being the only reason she joined was because she wanted to search for her mother) she answered with a simple statement. _

_"I quit. I will just give up on being a Team Rocket." said an upset Jessie. "I think it was a great idea for Team Rocket." replied a voice from behind them. Jessie and Meowth turned around and was shocked to see James without a scratch. _

_"What you mean about quitting the job at Team Rocket?"_

_"Because it's too dangerous. I've been thinking about myself for quitting or just staying at headquarters. I chose quitting, because I never knew everything about being serious. Jessie, Meowth, would you like to join me and run away from this place?". Both of them were very shocked to hear his question._

_"...Okay let do it"_

_James smiled, as the trio were successful in leaving without their boss noticing. They also put some clothes and food for the journey._

_End of Flashback_

"It wasn't very easy to decide about leaving or staying." James thinking about those good memories.

"Don't forget about meeting with Professor Oak."

_Flashback_

_The three had arrived at Oak's Lab to get their own Pokedexes. The Professor was surprised to see a new trainer come in with a walking Meowth._

_"What are you doing at my lab and how can your Meowth walk?"_

_"It is a very long story." replied Meowth, which left him speechless._

_"We're sorry for coming in your lab, Professor, we just wanted to get a PokeDex", said James. _

_The trio then told Professor Oak about their past, including the joining and quitting parts of being Rocket members. Professor Oak decided to keep the secret and handed them some new Pokedexes. _

_He asked about getting starter Pokemon, but Jessie and James already got Ekans and Koffing. The Trio decided to leave and head out on their new adventures._

_"Well, that was kind of easy to handle." said Jessie. Before James and Meowth could reply, a kid in his pajamas bumped into them._

_"Ouch! Sorry for bumping you guys, but can't talk right now!" the panicking boy got up and ran quickly to the lab. Jessie and James knew the answer to this: He is getting a late starter._

* * *

_We are the Team Rocket! Hand over all Pokémon now!" yelled a blonde haired female criminal._

_"No, you can't take my Pikachu away!" _

_"Okay you ask for it!" replied a turquoise haired male._

_"I think you shouldn't ask for it like that." said Jessie._

_Everybody turned around to see two people with their Meowth. A boy recognized them back when he was in hurry to the Oak Labs._

_"Who are you two and how can your Meowth can walk on two legs? " questioned a red haired girl. _

_"Our names are not important." said James._

_Both of them released their Pokémon. _

_"Alright kid, use our Pikachu's thundershock attack!"_

_Pikachu then lit up in yellow, before blasting them out of the Pokémon Center. "LOOKS LIKE TEAM ROCKET IS BLASTING OFF AGAIN!"_

_"Wow, thank you so much for saving us!" _

_Jessie and James both nodded and were about to leave. "Wait, I want to know why you guys helped us. "_

_"Sorry, we can't tell you about us kid."_

_They then left without another word._

_After the boy caught his second Pokémon, Jessie and James somehow met up with them again. They decide to have a battle of 3 on 3. His Caterpie was the last Pokémon standing, and had successfully defeated them in his first battle, which caused it to evolve into a Metapod._

_"Congratulations on winning your first battle and having your Caterpie evolve into Metapod." said a smiling Meowth._

_"Thank you for the battle with me. My name is Ash Ketchum from Pallet Town."_

_"My name is Misty Waterflower."_

_"I'm Jessie, nice to meet you."_

_"James is the name." They all decided to travel together._

"Wobbufet!(Jessie, James, Ash is winning the league!)" cried a happy Wobbuffet. The trio rushed to the living room, and saw Ash winning the Unova League. All of their Pokémon were watching to see Ash in the league.

"Wow, this is a lot different from Ash back then."

"Yeah, it wasn't very easy to say goodbye."  
_  
Flashback_

_After leaving Dawn and Brock from Sinnoh, Ash and his friends finally made it home._

_"Man, it's been awhile since I was home, right Pikachu?"_

_"Ash, it been so long. I'm glad to see you back home from the journey." cried a smiling Delia._

_Ash hugged his mom and asked where Tracey and Professor Oak were. They were at the lab doing some research she said. After Ash and his friends were done eating, they headed to the Laboratory._

_When they all arrived at the Lab, they saw Professor Oak talking to Professor Jupiter in Unova. Tracey was talking about a new Pokémon that had never been seen in any other regions._

_Ash and Pikachu were very excited about going to the Unova Region and challenging any gym battles and new Pokémon. Jessie and James decided to go to Johto to compete in contests and become a breeder._

_"I guess this is it." said a sad Jessie._

_"Yeah, we're really sorry for not telling you earlier with our friends, Brock and Dawn."_

_"Hey, cheer up,this is your dream. You're becoming a Pokémon breeder and being a top coordinator!" said a reluctant, yet happy Ash._

_They each gave a handshake and hug to each other. Ash got in Oak's car, both of them waving goodbye._

_End of the Flashback_

After the Trio was done with their memories, Jessie, James, Meowth, and their Pokémon got a phone call from Misty and said they're having a party for Ash at the Oak's Lab. Both then agreed, ready to see Ash again.

* * *

** really sorry if this chapter a little boring, but I just want to include a explain about Jessie and James. I apologize about last chapter for puting the last-minute on the list. **

**I decide to do Gymshipping, Wishfulshipping, and Showoffshipping (Sorry if you are the fan of any shipping with Dawn). Here the list and nothing very new.**

**For Zoey: ShootDownshipping (Kenny x Zoey), Againstshipping (Paul x Zoey) or Emulateshipping (Barry x Zoey)**

**For Georgia: Hairflipshipping (Drew x Georgia), OverArrogantshipping (Paul x Georgia) or Georgia x Trip**

**For Burgundy: Burgundy x Paul, Burgundy x Drew or Burgundy x Trip**

**For Ursula: Mockshipping (Paul x Ursula), Egocentricshipping (Harley x Ursula) or Conway x Ursula**

**For Solidad: Defeatedshipping/Gossipshipping (Drew x Solidad), KantoContestshipping (Harley x Solidad) or Nando x Solidad**

**For Bianca: Spokeshipping (Stephan x Bianca), Hypershipping (Barry x Bianca) or Trip x Bianca**

**Also should I include Handymanshipping (Tracey x Daisy) and Ritchie x Casey ?**

**I still need more vote, so I can post a final shipping in next chapter. If you have any questions, please review.**


End file.
